A. Okamoto, D. Arnold
Aug 1, 1985
Citations
0
Influential Citations
15
Citations
Journal
Canadian Journal of Chemistry
Abstract
The photosensitized (electron transfer) carbon–carbon bond cleavage of 1,1,2,2-tetraphenylethane (1b), 2-(4-methoxy-phenyl)-1,1-diphenyl-2-niethylpropane (1c), 1,1,2-triphenyl-2-methylpropane (1d), and 2-(4-trifluoromethylphenyl)-1,1-diphenyl-2-methylpropane (1e) has been studied with 1,4-dicyanobenzene (2) serving as the electron-accepting sensitizer. The oxidation potential of 1b–e have been measured by cyclic voltammetry. Estimation of the free-energy associated with the electron transfer between these donors (1b–e) and the first excited singlet state of 2, using the Weller equation, indicates the process is favorable in every case. There is, in every case, a one-to-one correspondence of products derived from reaction of the carbocation fragment and from the carbanion derived from the initially formed radical fragment. The efficiency of the reaction of 1b, which gives a good yield of diphenylmethane (3) and methyl diphenylmethyl ether, has been studied as a function of temperature. The observed activat...